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Just wanted to add my two cents as someone who's been filing Schedule C for my side business for 7 years. The "at risk" question confused me too at first, but it's really aimed at catching people involved in tax shelters. For regular small business owners (Etsy, freelancing, consulting, etc.), your investment is almost always "at risk" because you could lose the money you put in. The only time you'd answer "No" is if you have some arrangement where someone else guaranteed your investment or where you're not personally liable for business debts beyond your initial investment (like certain limited partnerships). If you put your own money in and could lose it if the business fails, just check "Yes" and move on!
Dylan Fisher
ā¢What about equipment I bought for my business that I could still sell if the business fails? Is that still considered "at risk"?
Yes, that equipment is still considered "at risk" even if you could potentially sell it later. The question is really asking if you could potentially lose the money you invested, not if you definitely will lose it. For example, if you bought a $2,000 computer for your business, it starts depreciating immediately and you might only get $800 if you had to sell it used. That potential for loss makes it "at risk." The IRS is trying to distinguish normal business investments from certain tax shelter arrangements where investors are protected from any possibility of loss.
Edwards Hugo
Just wanted to throw in my experience. Last year I messed up and left line 32 blank on my Schedule C because I didn't understand it. Got a letter from the IRS about 3 months later asking me to clarify. Wasn't a big deal - just had to respond saying "Yes" all investments were at risk (since I just had a simple freelance writing business with my laptop and some software). But it delayed my refund by about 6 weeks, so definitely worth just answering it correctly the first time!
Gianna Scott
ā¢Did you have to file an amended return or was just responding to the letter enough?
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I'm in a similar situation and my accountant recommended calculating the additional tax myself using the tax brackets. For example, if your first job puts you in the 22% bracket, and your second job pushes you partly into the 24% bracket, calculate how much of that second income will be taxed at 24% vs 22%, then figure out how much extra you need withheld per paycheck. You can also do a "catch-up" amount if you're starting the second job mid-year by dividing the additional tax by the number of remaining pay periods.
Yara Haddad
ā¢Could you explain how to actually calculate this with an example? I'm trying to do this math myself but getting confused about where the bracket cutoffs are and how to determine the additional amount needed.
Sure! Let's use 2024 tax brackets for a single filer as an example. The 22% bracket goes from $44,726 to $95,375, and the 24% bracket is $95,376 to $182,100. If your first job pays $85,000, you're already in the 22% bracket. When you add $55,000 from the second job, your total is $140,000. So $95,375 - $85,000 = $10,375 of your second job income is still in the 22% bracket, and the remaining $44,625 is in the 24% bracket. The additional tax you'd owe is: $10,375 Ć 22% = $2,282.50, plus $44,625 Ć 24% = $10,710. Total extra tax of $12,992.50. If you're paid biweekly (26 paychecks), you'd need about $500 extra withheld per paycheck to cover this. You could either check the multiple jobs box on one W-4 or add an additional amount to Step 4(c).
Has anyone used the IRS Tax Withholding Estimator for multiple jobs? I tried it last year and found it super confusing. It kept asking for YTD withholding info I didn't have handy.
Paolo Conti
ā¢I use it regularly and find it pretty accurate, but you definitely need your paystubs and last year's tax return handy. The key is entering the information exactly as requested. For the second job, you can enter the expected annual salary and $0 for withholding so far if you haven't started yet. The estimator will then tell you exactly what to put on each W-4. I've found it gets me within $100 of my actual tax bill every year.
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Ev Luca
Pro tip: If u have simple taxes, try the IRS direct file pilot program this year! Totally free and handles W2s and basic 401k distributions. I used it and it took like 20 mins start to finish. Only downside is its only available in certain states right now. Check if ur eligible here: https://directfile.irs.gov/ TurboTax is straight robbing people now smh
Avery Davis
ā¢Which states is it available in? I'm in Florida and would love to try this!
Ev Luca
ā¢It's available in 12 states for 2024 filing season: Arizona, California, Florida, Massachusetts, Nevada, New Hampshire, New York, South Dakota, Tennessee, Texas, Washington, and Wyoming. They're planning to expand it next year if the pilot goes well. If you're in Florida, you're in luck! Definitely check it out. Super simple interface and you're filing directly with the IRS so no middleman taking a cut.
Happened to me to!!! Try H&R Block online, they usually have better free options than TurboTax. My husband and I used them last yr after TT tried to charge us $89 for a simple return with a HSA. H&R did it free!!
Are you sure H&R Block is still free for 401k stuff? I just tried them and they wanted to upgrade me to "Deluxe" for $55 when I entered my 1099-R.
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Make sure your subcontractor knows he needs to file Schedule C and Schedule SE with his tax return. Those are the forms for self-employment income and self-employment tax calculation. Also, he should track ALL his business expenses - miles driven, tools purchased, insurance, phone use for business, even a portion of home internet if used for business. These deductions can really reduce his taxable income. A friend of mine doing construction subcontracting saved over $4,000 in taxes last year just by properly tracking and deducting legitimate business expenses!
Mei Wong
ā¢Do you have a simple system for tracking expenses? I always mean to keep good records but end up with a shoebox full of receipts at tax time lol.
I use a combination of a dedicated credit card for all business purchases and a simple spreadsheet. The credit card gives me electronic records for most expenses, while the spreadsheet is for tracking mileage and cash purchases. There are also some good apps specifically for contractors that let you snap pictures of receipts on the go and categorize them immediately. Much better than the shoebox method! Even just taking photos of receipts with your phone and organizing them into folders by month is better than nothing.
As someone who's been a construction subcontractor for years, tell him he's probably overthinking this. Yes, taxes on 1099 income can be significant, but the deductions in construction work are HUGE. If he's smart about tracking expenses (vehicle, tools, supplies, insurance, phone, even some clothing and meals), he'll likely only end up paying effective tax of 20-25% on what's left after deductions. I've been doing this for 15 years and rarely pay more than that percentage on my 1099 income.
Liam McGuire
ā¢This matches my experience too. The first year I paid way too much because I didn't track expenses well. Now I pay way less because I deduct everything legitimate. What tax software do you use? I've been using TurboSelf-Employed but wondering if there's something better for construction specifically.
Diego Vargas
19 Don't forget about keeping a detailed gambling diary/log! In addition to the statements others mentioned, the IRS actually expects you to maintain a contemporaneous log of your gambling activity. Include: - Date and type of gambling - Name and address of gambling establishment - Names of other people with you when gambling (if applicable) - Amount won or lost I learned this the hard way during an audit a few years back. Even with casino statements, they wanted to see my personal records too. Start keeping one now for any future gambling, and try to reconstruct as best you can for this year!
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Diego Vargas
ā¢3 Is there a specific format the IRS requires for this gambling log? Can I just create a spreadsheet or do they want something more formal? Seems like a lot of work to track every single bet.
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Diego Vargas
ā¢19 There's no official IRS form for the gambling log, so a spreadsheet works perfectly fine. The key is consistency and detail. For occasional gamblers, it's not too burdensome, but I understand it can be a lot if you gamble frequently. For high-volume bettors like sports gamblers, most online platforms allow you to download your complete betting history, which the IRS will generally accept if it contains the necessary details. The personal log becomes more important for cash games and situations where electronic records aren't automatically generated. The IRS mainly wants to see that you're tracking your activity in a systematic way.
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Diego Vargas
11 Just an important point nobody's mentioned - those W-2G forms from the raffle will be reported directly to the IRS, but your losses won't be unless you report them. Make absolutely sure your reported winnings match what's on the W-2G exactly, or you'll get an automatic mismatch letter from the IRS. Also, I found out last year that even if you itemize and deduct all your losses, the full amount of your gambling winnings still counts toward your AGI (Adjusted Gross Income), which can affect things like your Medicare premiums, social security taxation, and various tax credits. Something to be aware of!
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Diego Vargas
ā¢25 Wait, so you're saying even if I deduct $15k in losses against my $82k win, my AGI still goes up by the full $82k? That seems really unfair!
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